Hugh Hefner Regrets Not Marrying Holly Madison

Hugh Hefner Holly Madison

After being dumped at the altar by Crystal Harris, Hef tells friends, "I should have married Holly."

Even though Hugh Hefner has supposedly jumped into the arms of another Playmate (reportedly Anna Sophia Berglund) to help him get through the pain of having been dumped (practically) at the altar by ex-fiancee Crystal Harris, Hef is reportedly feel a bit wistful about one of his exes: Holly Madison.

Holly, who was Hef's number one girlfriend during The Girls Next Door phase of the Playboy CEO's life, made it no secret that she had wanted to marry him and have his kids while they were together. (She even reportedly paid for her own fertility treatments to try to get pregnant.)

And now that Hef has seen how supposedly cold and calculating Crystal has been about their breakup (some speculate that she merely used Hugh to jump-start her 15 minutes of fame,) Hef has been reportedly telling friends, "I should have married Holly." Hugh Hefner Isn't 'Nervous At All' About Marrying Crystal Harris

However, sadly for him, according to HollywoodLife.com, 32-year-old Holly, who now stars in her own reality show about her life as a Vegas showgirl called Holly's World, has moved on from her Playboy past, and sources close to her say that there isn't any chance for a reunion between the couple.

"That chapter of her life is closed," said a pal, noting that Holly is currently dating a nightclub owner named Jesse Waits, (whom we're guessing is much closer to her age.) Holly Madison Wants A Baby. Hef Just Wants Holly.

So is Holly the one that got away from Hef? It sure seems like it, especially since she reportedly stopped by the Playboy Mansion to lend her support to Hef after she learned of his breakup and even now seems to still be a caring friend. (Holly was even wary of Crystal's intentions from the start, although it was easy for everyone to chalk that up to jealousy at the time.)

Still, you never know what could happen in the future. And Hef certainly has his own special way of wooing the ladies. Holly Madison Is Upset About Hugh Hefner's Engagement

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